Paul Grieco - Academia.edu (original) (raw)

Papers by Paul Grieco

The use of water as a medium for promoting organic reactions has, for the most part, been non-exi... more The use of water as a medium for promoting organic reactions has, for the most part, been non-existent, despite the fact that water has served, and continues to serve, as the solvent in which the vast majority of biochemical processes take place. Chemists have only recently ...

Tetrahedron Letters, 1975

Journal of the American Chemical Society, 1969

Journal of the American Chemical Society, 1977

A total synthesis of 12-methylprostaglandin A2 (1) and 12-methylprostaglandin Fz,, (2) starting f... more A total synthesis of 12-methylprostaglandin A2 (1) and 12-methylprostaglandin Fz,, (2) starting from norbornadiene is reported. The preparation of the synthetic intermediate anti-7-methyl-2-bromo-5,5-ethylenedioxybicyclo[ 2.2. I ] heptane-7carboxylic acid methyl ester (7) is described in detail as well as its conversion to sesquifenchene (20) which confirms the CY orientation of the methyl group in the 12-methylprostaglandins. Prostaglandins represent an intriguing class of highly active mammalian3 hormones which may well be responsible for mediation of many physiological r e~p o n s e s .~ One of the problems with the natural prostaglandins is that they are rapidly metabolized (deactivated) in man. Some time ago Samuelsson5 demonstrated that oxidation of the allylic C-15 alcohol followed by reduction of the Al3,I4 double bond constituted a rapid mode of deactivation. This problem has been dealt with by the Upjohn group through introduction of a methyl group a t C-15.6 In addition to oxidation a t C-15, /3oxidation of the carboxyl side chain and w-oxidation of the alkyl side chain represent further metabolic pathway^.^.'

International Journal of Plant Sciences, 1999

Glaucarubolone, a naturally occurring quassinoid from the root bark of Castela polyandra, Simarou... more Glaucarubolone, a naturally occurring quassinoid from the root bark of Castela polyandra, Simaroubaceae, with a C(8), C(11) hemiacetal bridge, is demonstrated to be a potent inhibitor of both the auxin‐induced component of the plasma membrane NADH oxidase and of plant cell enlargement in soybean (Glycine max), Arabidopsis (Arabidopsis thaliana), tomato (Lycopersicum esculentum), and Sorghum (Sorghum vulgare). Auxin‐stimulated NADH oxidase activity of isolated vesicles of soybean, A. thaliana, and tomato plasma membranes were inhibited half maximally by ca. 0.1 nM glaucarubolone. Auxin‐induced enlargement of stem segments of soybean and elongation growth of A. thaliana seedlings were inhibited half maximally by ca. 10 nM glaucarubolone with significant inhibition of auxin‐stimulated growth even at nannomolar glaucarubolone concentrations. Seedlings of A. thaliana and tomato treated with sublethal concentrations of 1–10 μM glaucarubolone remained alive but failed to elongate for periods of two to several months. Once seedlings recovered from the effects of the inhibitor, they resumed growth, flowered, and produced fruits. Treated A. thaliana produced viable seeds that germinated and developed into normal‐appearing progeny. In contrast to glaucarubolone, which inhibited preferentially auxin‐induced growth and plasma membrane NADH oxidase, simalikalactone D, a quassinoid with a C(8), C(13) epoxymethano bridge, inhibited the constitutive NADH oxidase activity and growth and had little or no effect on the 2,4‐D‐responsive NADH oxidase and growth. The findings provide correlative evidence for a functional role of both the constitutive and the auxin‐stimulated plasma membrane NADH oxidase activities in plant cell enlargement.

Journal of Synthetic Organic Chemistry, Japan, 2000

The RAND Journal of Economics

ChemInform

Carbocyclic Ring Construction via an Intramolecular Diels-Alder Reaction of an in situ-Generated,... more Carbocyclic Ring Construction via an Intramolecular Diels-Alder Reaction of an in situ-Generated, Heteroatom-Stabilized Allyl Cation: Total Synthesis of (±)-Lycopodine.-The title compound (X) is totally synthesized using a [4 + 2] cycloaddition leading to the tricyclic compound (VI) possessing all the necessary C atoms needed for the elaboration of (X), radical cyclization leading to the exclusive formation of (VIII) containing the correct stereocenter at C-15, and a Stieglitz rearrangement to establish the bridgehead N atom as the key steps.-(GRIECO,

Pest management science, 2018

Semiochemicals for monitoring, attracting or repelling pest and beneficial organisms are increasi... more Semiochemicals for monitoring, attracting or repelling pest and beneficial organisms are increasingly deployed in agricultural and forest systems for pest management. However, the use of aggregation pheromones and host-plant attractants for the express purpose of increasing the efficacy of classical biological control agents of weeds has not been widely reported. Therefore, we conducted field-based assays to determine if a specialized wax-based matrix impregnated with an aggregation pheromone of the northern tamarisk beetle Diorhabda carinulata (Desbrochers) or host-plant volatiles could increase the efficacy of D. carinulata. The aggregation pheromone and host-plant volatiles were formulated for field application using a wax-based matrix. Reported release rates suggest that this matrix is a viable formulation for enhancing D. carinulata aggregations under field conditions. Pheromone-treated saltcedar plants (Tamarix spp.) not only had higher densities of adult and larval D. carinul...

J. Chem. Soc., Chem. Commun.

Journal of the Chemical Society, Chemical Communications

Tetrahedron Letters

ABSTRACT Lithium perchlorate in diethyl ether catalyzes the cyclocondensation of N-BOC protected ... more ABSTRACT Lithium perchlorate in diethyl ether catalyzes the cyclocondensation of N-BOC protected α-amino aldehydes with 1-methoxy-3-tert-butyldimethylsilyloxybutadiene providing, after exposure to acid, dihydropyrones possessing the threo configuration.